With notable exception (Avery & Jablin, 1988), the role of communication during retirement planning has not been studied in organizational communication research. In light of the extant research on information seeking in organizations, and since retirement is an organizational disengagement process, this analysis seeks to shed light on the antecedents, covariates, and outcomes of information acquisition during retirement planning. First, drawing from organizational socialization research, retirement information seeking was explored, yielding four research questions about the information sources and types, timing, and communication tactics employed. Using role ambiguity research and uncertainty reduction theory (URT; Berger & Calabrese, 1975; Berger & Bradac, 1982), this analysis proposed three hypotheses that confirmed uncertainty during retirement planning and link it to information-seeking behavior. Adopting Bandura’s (1977; 1986; 1997) theory of social cognition—specifically focusing on self-efficacy—perceived preparedness or readiness to retire was predicted in five hypotheses to be associated with retirement information-seeking behavior and retirement uncertainty. Finally, combining URT and Bandura’s self-efficacy, the role of retirement self-efficacy, as a psychological driver in the relationship between information-seeking behavior and retirement-related outcomes, was predicted in the final six hypotheses. Two focus groups and a total of 207 questionnaires from a representative sample of high school teachers revealed that communication in the form of information seeking plays an important role in planning for retirement. This study found that among the multiple sources, types, and tactics of retirement information seeking, employees seek direct information about their financial future from coworkers and a retirement specialist upon approaching 55 years of age. As expected, a relationship between retirement uncertainty, retirement information seeking, and retirement self-efficacy exists. However, the predictive potential of information seeking was found to be associated though not mediated by self-efficacy, raising questions about a possible recursive relationship between information seeking and self efficacy. Additional implications of these findings are discussed in terms of exploring the use of URT to explain retirement planning, retirement planning as a role-exit transition, the similarities and differences between retirement-disengagement and organizational socialization research, and communication-aging dynamics relevant to the retirement transition.